WO2015115962A1 - Synthesis of amonnium dinitramide, adn - Google Patents
Synthesis of amonnium dinitramide, adn Download PDFInfo
- Publication number
- WO2015115962A1 WO2015115962A1 PCT/SE2015/000004 SE2015000004W WO2015115962A1 WO 2015115962 A1 WO2015115962 A1 WO 2015115962A1 SE 2015000004 W SE2015000004 W SE 2015000004W WO 2015115962 A1 WO2015115962 A1 WO 2015115962A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- ammonium
- adn
- alcohol
- gudn
- dinitramide
- Prior art date
Links
- MJVUDZGNBKFOBF-UHFFFAOYSA-N n-nitronitramide Chemical compound [O-][N+](=O)N[N+]([O-])=O MJVUDZGNBKFOBF-UHFFFAOYSA-N 0.000 title claims description 3
- 230000015572 biosynthetic process Effects 0.000 title description 2
- 238000003786 synthesis reaction Methods 0.000 title description 2
- BRUFJXUJQKYQHA-UHFFFAOYSA-O ammonium dinitramide Chemical compound [NH4+].[O-][N+](=O)[N-][N+]([O-])=O BRUFJXUJQKYQHA-UHFFFAOYSA-O 0.000 claims abstract description 48
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 29
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 22
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 15
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims abstract description 15
- 235000011130 ammonium sulphate Nutrition 0.000 claims abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 9
- GEHMBYLTCISYNY-UHFFFAOYSA-N Ammonium sulfamate Chemical compound [NH4+].NS([O-])(=O)=O GEHMBYLTCISYNY-UHFFFAOYSA-N 0.000 claims abstract description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 6
- SQSPRWMERUQXNE-UHFFFAOYSA-N Guanylurea Chemical compound NC(=N)NC(N)=O SQSPRWMERUQXNE-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 4
- 238000000926 separation method Methods 0.000 claims abstract description 4
- 238000004519 manufacturing process Methods 0.000 claims description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 3
- CHBRHODLKOZEPZ-UHFFFAOYSA-N Clotiazepam Chemical compound S1C(CC)=CC2=C1N(C)C(=O)CN=C2C1=CC=CC=C1Cl CHBRHODLKOZEPZ-UHFFFAOYSA-N 0.000 claims 10
- 238000000034 method Methods 0.000 abstract description 25
- 239000000203 mixture Substances 0.000 abstract description 19
- 239000000706 filtrate Substances 0.000 abstract description 17
- 229940044197 ammonium sulfate Drugs 0.000 abstract description 13
- 239000002244 precipitate Substances 0.000 abstract description 11
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract description 8
- 229910052700 potassium Inorganic materials 0.000 abstract description 7
- 239000011591 potassium Substances 0.000 abstract description 7
- 239000002245 particle Substances 0.000 abstract description 6
- 239000002904 solvent Substances 0.000 abstract description 6
- 238000001914 filtration Methods 0.000 abstract description 4
- 238000001704 evaporation Methods 0.000 abstract description 2
- 230000008020 evaporation Effects 0.000 abstract description 2
- 239000012141 concentrate Substances 0.000 abstract 1
- 239000000356 contaminant Substances 0.000 abstract 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 30
- 239000012074 organic phase Substances 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 6
- 239000012530 fluid Substances 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000005342 ion exchange Methods 0.000 description 3
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 3
- 239000000446 fuel Substances 0.000 description 2
- KNIKDPRISVIPBU-UHFFFAOYSA-N 1,2-dichloro-4-[isocyano-(4-methylphenyl)sulfonylmethyl]benzene Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C([N+]#[C-])C1=CC=C(Cl)C(Cl)=C1 KNIKDPRISVIPBU-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical class CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- XSUZSAMSJKGENR-UHFFFAOYSA-N nitramide;potassium Chemical compound [K].N[N+]([O-])=O.N[N+]([O-])=O XSUZSAMSJKGENR-UHFFFAOYSA-N 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 229940093932 potassium hydroxide Drugs 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B21/00—Nitrogen; Compounds thereof
- C01B21/082—Compounds containing nitrogen and non-metals and optionally metals
- C01B21/087—Compounds containing nitrogen and non-metals and optionally metals containing one or more hydrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C06—EXPLOSIVES; MATCHES
- C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
- C06B25/00—Compositions containing a nitrated organic compound
- C06B25/34—Compositions containing a nitrated organic compound the compound being a nitrated acyclic, alicyclic or heterocyclic amine
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/10—Selective adsorption, e.g. chromatography characterised by constructional or operational features
- B01D15/20—Selective adsorption, e.g. chromatography characterised by constructional or operational features relating to the conditioning of the sorbent material
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/10—Selective adsorption, e.g. chromatography characterised by constructional or operational features
- B01D15/22—Selective adsorption, e.g. chromatography characterised by constructional or operational features relating to the construction of the column
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/02—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material
- B01J20/20—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising free carbon; comprising carbon obtained by carbonising processes
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B21/00—Nitrogen; Compounds thereof
- C01B21/082—Compounds containing nitrogen and non-metals and optionally metals
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2220/00—Aspects relating to sorbent materials
- B01J2220/50—Aspects relating to the use of sorbent or filter aid materials
- B01J2220/52—Sorbents specially adapted for preparative chromatography
Definitions
- ADN ammonium dinitramide
- PDN potassium-dinitramide
- US7981393 KDN is reacted with ammonium- sulfate in a water solution which yields ADN.
- the second process stage is described in EP0843647.
- a problem with this production is that the process includes potassium. The potassium will be left in the final product, ADN, which is a problem. It is difficult and expensive to remove the potassium from the ADN. Potassium presents an increased signature when combusting solid rocket fuels and in liquid fuels it creates problems with catalyst poisoning.
- Another problem with the current production process is that the process involves two process steps. Additional process steps create a more
- a further problem with using the current process is that it demands the use of a large amount of solvent. Solvents have to be taken care of, and possess an environmental burden which preferably should be avoided. The current process is hence expensive, time consuming, environmentally burdening and yields ADN that can be polluted by potassium.
- the invention comprises a process by which ADN can be produced using GUDN.
- GUDN is reacted with an ammonium source, for example ammonium- sulfate, ammonium-sulfamate or ammonia, where an ion-change forms ADN from GUDN in a single process stage.
- an ammonium source for example ammonium- sulfate, ammonium-sulfamate or ammonia
- an ion-change forms ADN from GUDN in a single process stage.
- the invention is comprises reacting GUDN with an ammonium source whereby ADN is formed through an ion-exchange reaction.
- GUDN is heated together with an ammonium source, for example ammonium-sulfate or ammonium-sulfamate in a water solution until the solution is homogenous. Thereafter the heat source is removed and alcohol, for instance methanol, ethanol, propanols, butanols or similar is added when guanylurea-sulfate (when using an ammonium source, for example ammonium-sulfate or ammonium-sulfamate in a water solution until the solution is homogenous. Thereafter the heat source is removed and alcohol, for instance methanol, ethanol, propanols, butanols or similar is added when guanylurea-sulfate (when using an ammonium source, for example ammonium-sulfate or ammonium-sulfamate in a water solution until the solution is homogenous. Thereafter the heat source is removed and alcohol, for instance methanol, ethanol, propanols, butanols or similar
- ammonium-sulfate or guanylurea-sulfamate (using ammonium-sulfamate) precipitates from the solution and is filtered off.
- a filtrate is achieved that, among other things contains ADN and un-reacted GUDN.
- the filtrate is concentrated and the residue from this stage is suspended in one of the above mentioned alcohols, and ADN is dissolved in it. GUDN remains undissolved and is discarded through filtration.
- the filtrate is concentrated to dryness which yields pure ADN.
- ammonia is used as a source of ammonium.
- a solution of ammonia and GUDN is made.
- an ion-exchange takes place at which ADN and guanylurea is formed in the solution.
- the solution is passed through a column with active carbon which has been pre-treated with diluted ammonia. Guanylurea then remained in the column and ADN leaves the column together with the solvent. Evaporation of this, so called, eluted solution yields pure ADN.
- GUDN and ammonium-sulfate are mixed in an alcohol, for example methanol, ethanol, propanols and butanols or similar.
- a mixture of alcohol, GUDN and ammonium-sulfate is backflow-boiled to achieve an ion-exchange. Thereafter the mix is left to cool and a precipitate is formed. The precipitate is filtered off and a filtrate is achieved.
- the filtrate there is, among other things, ADN and un-reacted GUDN.
- the filtrate is concentrated to dryness and the remains from this stage is suspended in one of the above mentioned alcohols, at which time ADN is dissolved.
- GUDN remains un-dissolved and is removed through filtration.
- the filtrate which is achieved is concentrated to dryness yielding pure ADN.
- GUDN is mixed with ammonium-sulfate in a solution of water and alcohol.
- Alcohols that can be used are, for example, propanols, pentanols or similar so that a two-phase system is achieved.
- the mixture is heated until a homogenous solution is achieved. Thereafter the heat is removed and the phases separate again.
- the organic phase is taken aside.
- the water phase is extracted using one of the above mentioned alcohols. After separation the organic phase from this extraction is mixed with the organic phase from the previous step. This mixture is concentrated to dryness which yields pure ADN.
- a mixture was made consisting of GUDN (1g, 4,78 mmole), ammonium- sulfate (0,758g, 5,74 mmole) and water (10 g). The mixture was heated to about 00° C while stirring until it was homogenous, in other words about 5 minutes. Thereafter the heat source was removed and 2-propanol (100 ml) was added which produced a precipitate. The precipitate was filtered and washed with 2-propanol (50 ml). The filtrate and the wash fluid were then mixed and concentrated to dryness. The remains from this stage was suspended in 2-propanol (100 ml) and the unsolved particles were filtered off. The filtrate from this stage was concentrated which yielded ADN. The return was 0,470 g (79,2%).
- a mixture was made consisting of GUDN (1g, 4,78 mmole), ammonium- sulfate (0,758g, 5,74 mmole) and water (10 g). The mixture was heated to about 100° C while stirring until it was homogenous, in other words about 5 minutes. Thereafter the heat source was removed and 2-propanol (200 ml) was added. Approximately 150 ml of the solvent was removed from the mixture through rotary evaporation under vacuum. The remainder from this concentrating stage was filtered. The precipitate that was filtered off was washed with 2-propanol (50 ml). This wash fluid was mixed with the filtrate. The mixture was concentrated which yielded ADN. The return was 0,327 g (55,1%).
- a mixture was made consisting of GUDN (1g, 4,78 mmole), ammonium- sulfate (0,758g, 5,74 mmole), water (5 ml) and 2-butanol (10 ml).
- the mixture was heated to about 100° C while stirring until it was homogenous, in other words about 5 minutes. Thereafter the heat source was removed.
- the solution then separated into an organic phase and a water phase.
- the organic phase and the water phase were parted.
- the water phase was extracted using 2-butanol (50 ml), when the solution separated into an organic phase and a water phase.
- the organic phases from the two separations were combined and concentrated which yields ADN .
- the return was 0,160 g (26,9%).
- a mixture was made consisting of GUDN (1g, 4,78 mmole), ammonium- sulfate (0,758g, 5,74 mmole) and methanol (50 ml). The mixture was backflow-boiled for 2 hours whereafter the heat source was removed. The unsolved particles were filtered away and washed with 2-propanol (50 ml). The filtered off reaction solution was mixed with the wash fluid. This mixture was then concentrated to dryness. The filtrate and the wash fluid were then mixed and concentrated to dryness. The remains from this step was suspended in 2-propanol (100 ml) and the unsolved particles were filtered away. The filtrate was concentrated which yielded pure ADN. The return was 0,145 g (24,4%).
- a column was filled with activated carbon (20 g). The carbon was rinsed with diluted ammonia (5% NH3 aq). A solution was made using GUDN (1 ,5 g, 7,17 mmole) and NH 3 (6 g, 25% aq). The solution was applied on the column, which then was eluated using diluted ammonia (5 % NH 3 aq). The obtained eluent was then concentrated to dryness which yielded ADN. The return was 0,667 g (75%)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Analytical Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP15743454.9A EP3099652B1 (de) | 2014-01-30 | 2015-01-29 | Synthese von ammoniumdinitramid (adn) |
US15/115,743 US10112834B2 (en) | 2014-01-30 | 2015-01-29 | Synthesis of ammonium dinitramide, ADN |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SE1400043-4 | 2014-01-30 | ||
SE1400043A SE537747C2 (sv) | 2014-01-30 | 2014-01-30 | Syntes av ammoniumdinitramid, ADN |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2015115962A1 true WO2015115962A1 (en) | 2015-08-06 |
Family
ID=53757416
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/SE2015/000004 WO2015115962A1 (en) | 2014-01-30 | 2015-01-29 | Synthesis of amonnium dinitramide, adn |
Country Status (4)
Country | Link |
---|---|
US (1) | US10112834B2 (de) |
EP (1) | EP3099652B1 (de) |
SE (1) | SE537747C2 (de) |
WO (1) | WO2015115962A1 (de) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SE541421C2 (en) * | 2017-06-01 | 2019-09-24 | Foi Grindsjoens Forskningscentrum | Synthesis of Ammonium Dinitramide (ADN) |
WO2020060451A1 (en) | 2018-09-17 | 2020-03-26 | Totalförsvarets Forskningsinstitut | Synthesis of ammonium dinitramide (adn) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111228855A (zh) * | 2020-01-14 | 2020-06-05 | 无锡市疾病预防控制中心 | 一种菠萝肉基质生物炭填料固相萃取柱的制备方法 |
CN113880112B (zh) * | 2021-11-03 | 2023-10-31 | 中国科学院大连化学物理研究所 | 一种制备二硝酰胺铵水溶液的方法 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0843647A1 (de) * | 1995-08-08 | 1998-05-27 | Försvarets Forskningsanstalt | Verfahren zur herstellung von dinitramidsäure und dinitramidsalze |
US7981393B2 (en) * | 2004-01-21 | 2011-07-19 | Försvarets Materielverk | Method of producing salts of dinitramidic acid |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5316749A (en) * | 1991-07-30 | 1994-05-31 | Sri International | Process for forming ammonium dinitramide salt by reaction between ammonia and a nitronium-containing compound |
US6117255A (en) * | 1998-07-28 | 2000-09-12 | Trw Inc. | Gas generating composition comprising guanylurea dinitramide |
-
2014
- 2014-01-30 SE SE1400043A patent/SE537747C2/sv unknown
-
2015
- 2015-01-29 WO PCT/SE2015/000004 patent/WO2015115962A1/en active Application Filing
- 2015-01-29 EP EP15743454.9A patent/EP3099652B1/de active Active
- 2015-01-29 US US15/115,743 patent/US10112834B2/en active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0843647A1 (de) * | 1995-08-08 | 1998-05-27 | Försvarets Forskningsanstalt | Verfahren zur herstellung von dinitramidsäure und dinitramidsalze |
US7981393B2 (en) * | 2004-01-21 | 2011-07-19 | Försvarets Materielverk | Method of producing salts of dinitramidic acid |
Non-Patent Citations (1)
Title |
---|
TALAWAR M. B.; ET AL.: "Environmentally compatible next generation green energetic materials (GEMs) ''.", JOURNAL OF HAZARDOUS MATERIALS, vol. 161, no. 2-3, 30 January 2009 (2009-01-30), pages 589 - 607, XP025681875 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SE541421C2 (en) * | 2017-06-01 | 2019-09-24 | Foi Grindsjoens Forskningscentrum | Synthesis of Ammonium Dinitramide (ADN) |
WO2020060451A1 (en) | 2018-09-17 | 2020-03-26 | Totalförsvarets Forskningsinstitut | Synthesis of ammonium dinitramide (adn) |
Also Published As
Publication number | Publication date |
---|---|
SE537747C2 (sv) | 2015-10-13 |
US10112834B2 (en) | 2018-10-30 |
US20170008768A1 (en) | 2017-01-12 |
EP3099652A1 (de) | 2016-12-07 |
EP3099652A4 (de) | 2017-07-26 |
EP3099652B1 (de) | 2018-12-26 |
SE1400043A1 (sv) | 2015-07-31 |
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